Trifluoroacetic acid → [5-Cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acid

HRID 1188685Notes

Reaction equation

HRID 1188685 reaction equation
[C:1]([C:3]1[C:4]([C:23]([F:26])([F:25])[F:24])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15]C(C)(C)C)=[O:14])[C:7]([CH:20]1[CH2:22][CH2:21]1)=[CH:6]2)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:3]1[C:4]([C:23]([F:26])([F:25])[F:24])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7]([CH:20]1[CH2:22][CH2:21]1)=[CH:6]2)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 711086661,1-Dimethylethyl [5-cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetate

Product 1

HCID 67406028[5-Cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetic acidYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,1-dimethylethyl [5-cyano-2-cyclopropyl-4-(trifluoromethyl)-1H-indol-1-yl]acetate (Example 362A) (1.23 g, 4 mmol) in dry CH2Cl2 (10 mL) was added TFA (3.1 mL, 40 mmol) at rt. The mixture was stirred at rt overnight. Solvent and excess TFA were removed in vacuo. The residue was tritrated with Et2O-hexanes to afford the title compound (1.05 g, 85%): MS (ES) m/z 309 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo

Sources & evidence

ORD record
ord-49de194020644f5bbb250d7f6b390d3c
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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